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Cruises Starting and Ending in San Juan

Are you looking for a cruise starting and ending in San Juan? December is the most popular month to join a roundtrip cruise from San Juan and we have 221 departures available from nine of the world's leading cruise lines.
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67 Cruises (221 Cruise Departures)
8 Day Caribbean Cruise with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Ships: Norwegian Epic, Norwegian Viva
Departures: Dec 2024 to Apr 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Barbados (+2 more), Saint Lucia, Sint Maarten
Exclusive Solo Offer
INSIDE
$1,564
OCEANVIEW
$3,354
BALCONY
$2,176
SUITE
$2,481
From 1,564
View Trip
8 Day San Juan, Barbados & Beyond with Virgin Voyages
Cruise
 (4)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 01 March 2025
Countries Visited: Puerto Rico, Saint Martin, Saint Lucia, Barbados (+2 more), Martinique, Saint Kitts and Nevis
INSIDE
$2,326
OCEANVIEW
$2,375
BALCONY
$2,518
SUITE
$5,454
From 2,326
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 18 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Grenada (+2 more), Saint Vincent, Dominica
Exclusive Deal
INSIDE
$1,634
OCEANVIEW
$1,921
BALCONY
$2,248
SUITE
$3,680
Save 686
From 1,419
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Jun 2024 to Apr 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia (+1 more), Barbados
Exclusive Deal
INSIDE
$1,282
OCEANVIEW
$1,350
BALCONY
$2,059
SUITE
$2,676
Save 1,294
From 1,166
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8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 22 March 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+1 more), Barbados
Exclusive Deal
INSIDE
$1,741
OCEANVIEW
$1,932
BALCONY
$2,560
SUITE
$3,726
Save 696
From 1,499
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departures: Dec 2025 to Mar 2026
Countries Visited: Puerto Rico, Virgin Islands, Curacao, Aruba (+1 more), Bonaire
Exclusive Deal
INSIDE
$1,619
OCEANVIEW
$1,980
BALCONY
$2,491
SUITE
$3,733
Save 826
From 1,403
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 07 December 2025
Countries Visited: Puerto Rico, Bonaire, Curacao, Aruba (+1 more), Virgin Islands
Exclusive Deal
INSIDE
$1,485
OCEANVIEW
$1,771
BALCONY
$2,079
SUITE
$3,414
Save 615
From 1,297
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8 Day Saint (Isles) & Seas of the Caribbean with Virgin Voyages
Cruise
 (4)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ships: Resilient Lady, Valiant Lady
Departures: Dec 2024 to Mar 2026
Countries Visited: Puerto Rico, Virgin Islands, Barbados, Saint Lucia (+2 more), Antigua and Barbuda, Saint Martin
INSIDE
$2,035
OCEANVIEW
$2,191
BALCONY
$2,372
SUITE
$5,515
From 2,035
View Trip
9 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 13 April 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Kitts and Nevis (+2 more), Barbados, Dominica
Exclusive Deal
INSIDE
$1,868
OCEANVIEW
$2,304
BALCONY
$4,372
SUITE
$4,291
Save 746
From 1,640
View Trip
9 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 24 May 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Dominica (+2 more), Barbados, Saint Lucia
Exclusive Deal
INSIDE
$1,916
OCEANVIEW
$2,326
BALCONY
$3,459
SUITE
$3,772
Save 754
From 1,667
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15 Day Eastern Caribbean Voyage with Azamara Cruises
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ships: Azamara Onward, Azamara Quest
Departures: Nov 2025 to Dec 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+8 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Sint Maarten
INSIDE
$3,474
OCEANVIEW
$4,510
BALCONY
$5,545
SUITE
$7,856
From 3,474
View Trip
11 Day Turquoise Shores, Hidden Isles with Regent Seven Seas
Cruise

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 03 January 2025
Countries Visited: Puerto Rico, Grenada, Saint Vincent, Dominica (+5 more), Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Martinique, Saint Kitts and Nevis
Exclusive DealExclusive Solo Offer
INSIDE
-
OCEANVIEW
$7,554
BALCONY
$10,059
SUITE
$11,544
Save 4,316
From 7,554
View Trip
8 Day Southern Caribbean Cruise with Celebrity Cruises
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 30 November 2024
Countries Visited: Puerto Rico, Sint Maarten, Saint Lucia, Barbados (+2 more), Dominica, Antigua and Barbuda
Exclusive Offer
INSIDE
$1,435
OCEANVIEW
$1,623
BALCONY
$2,214
SUITE
$3,628
Save 2,655
From 1,435
View Trip
8 Day Antigua, Martinique, & Barbados & More with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 21 February 2026
Countries Visited: Puerto Rico, Sint Maarten, Barbados, Martinique (+2 more), Antigua and Barbuda, Virgin Islands
INSIDE
$2,240
OCEANVIEW
$2,496
BALCONY
$2,725
SUITE
$6,363
From 2,240
View Trip
15 Day An Extended Journey of Caribbean Culture and Tropical Trails with Explora Journeys
Cruise

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 21 February 2025
Countries Visited: Puerto Rico, Aruba, Curacao, Bonaire (+6 more), Trinidad and Tobago, Barbados, Saint Lucia, Martinique, Saint Vincent, Grenada
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$10,593
SUITE
$9,949
From 9,949
View Trip
13 Day Treasures Of Aruba, Bonaire & Curacao with Seabourn
Cruise

13 Days (12 Nights) San Juan to San Juan
Cruise Line: Seabourn
Ship: Ovation
Departure: 02 December 2025
Countries Visited: Puerto Rico, Aruba, Curacao, Bonaire (+6 more), Martinique, Dominica, Montserrat, Saint Kitts and Nevis, Antigua and Barbuda, Virgin Islands
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$7,585
SUITE
$15,243
From 7,585
View Trip
8 Day Aruban Sights & Antiguan Nights with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 03 January 2026
Countries Visited: Puerto Rico, Aruba, Curacao, Antigua and Barbuda (+1 more), Sint Maarten
INSIDE
$2,131
OCEANVIEW
$2,386
BALCONY
$2,616
SUITE
$6,120
From 2,131
View Trip
12 Day Cartagena, Aruba, Antigua & More with Virgin Voyages
Cruise

12 Days (11 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 10 February 2026
Countries Visited: Puerto Rico, Colombia, Curacao, Aruba (+1 more), Antigua and Barbuda
INSIDE
$3,497
OCEANVIEW
$3,930
BALCONY
$4,288
SUITE
$10,111
From 3,497
View Trip
8 Day Joy Of The Islands with Regent Seven Seas
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 13 January 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Dominica (+3 more), Saint Lucia, Antigua and Barbuda, Saint Barthelemy
Exclusive Solo OfferExclusive Deal
INSIDE
-
OCEANVIEW
$5,334
BALCONY
$7,254
SUITE
$8,581
Save 3,546
From 5,334
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Jewel of the Seas
Departures: Nov 2025 to Apr 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Dominica (+1 more), Barbados
Exclusive Deal
INSIDE
$1,379
OCEANVIEW
$1,557
BALCONY
$2,054
SUITE
$3,002
Save 771
From 1,198
View Trip
8 Day Sunny Miles of Tropical Isles with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Nov 2025 to Feb 2026
Countries Visited: Puerto Rico, Sint Maarten, Barbados, Saint Lucia (+2 more), Martinique, Saint Kitts and Nevis
INSIDE
$2,093
OCEANVIEW
$2,322
BALCONY
$2,552
SUITE
$5,950
From 2,093
View Trip
8 Day Valiant New Year's Ahoy! with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 27 December 2025
Countries Visited: Puerto Rico, Sint Maarten, Saint Kitts and Nevis, Saint Lucia (+2 more), Barbados, Virgin Islands
INSIDE
$3,111
OCEANVIEW
$3,468
BALCONY
$3,801
SUITE
$9,050
From 3,111
View Trip
8 Day Valiant Caribbean Holidays with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 20 December 2025
Countries Visited: Puerto Rico, Sint Maarten, Saint Kitts and Nevis, Antigua and Barbuda (+2 more), Saint Lucia, Virgin Islands
INSIDE
$2,501
OCEANVIEW
$2,807
BALCONY
$3,062
SUITE
$7,192
From 2,501
View Trip
8 Day Barbados, Antigua, BVI & More with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 24 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Barbados, Martinique (+2 more), Antigua and Barbuda, Sint Maarten
INSIDE
$2,138
OCEANVIEW
$2,393
BALCONY
$2,623
SUITE
$6,127
From 2,138
View Trip
8 Day Virgin Island Views & Saint Isle Blues with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 10 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Barbados, Saint Vincent (+1 more), Saint Kitts and Nevis
INSIDE
$2,127
OCEANVIEW
$2,382
BALCONY
$2,612
SUITE
$6,116
From 2,127
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Jewel of the Seas
Departure: 17 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Martinique (+1 more), Barbados
Exclusive Deal
INSIDE
$1,650
OCEANVIEW
$1,937
BALCONY
$2,243
SUITE
$3,518
Save 674
From 1,462
View Trip
8 Day Quaint Castries to Elegant Antigua with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 07 March 2026
Countries Visited: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Martinique (+2 more), Antigua and Barbuda, Virgin Islands
INSIDE
$2,231
OCEANVIEW
$2,487
BALCONY
$2,716
SUITE
$6,354
From 2,231
View Trip
8 Day Sunsets in the Lesser Antilles with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ships: Resilient Lady, Valiant Lady
Departures: Jan 2025 to Mar 2026
Countries Visited: Puerto Rico, Saint Kitts and Nevis, Martinique, Curacao (+1 more), Aruba
INSIDE
$1,945
OCEANVIEW
$2,174
BALCONY
$2,393
SUITE
$5,265
From 1,945
View Trip
8 Day Eternal Sunshine with Regent Seven Seas
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 30 January 2025
Countries Visited: Puerto Rico, Virgin Islands, Dominica, Saint Lucia (+2 more), Antigua and Barbuda, Saint Barthelemy
Exclusive Solo OfferExclusive Deal
INSIDE
-
OCEANVIEW
$5,334
BALCONY
$7,254
SUITE
$8,581
Save 3,546
From 5,334
View Trip
8 Day St. Kitts, Barbados, Martinique & More with Virgin Voyages
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 17 January 2026
Countries Visited: Puerto Rico, Saint Kitts and Nevis, Barbados, Martinique (+2 more), Antigua and Barbuda, Sint Maarten
INSIDE
$2,285
OCEANVIEW
$2,540
BALCONY
$2,796
SUITE
$6,514
From 2,285
View Trip
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